Monoazo dyestuffs soluble in water



Patented June 25, 1940 TENT 1- Erich Fischer, Bad Soden in Taunus,Germany, assignor to General Aniline & Film Corpora tion, a corporationof Delaware No Drawing. Application June 21, 1938, Serial a X1 aconcentrated aqueous solution of 69 parts of OH sodium nitrite beingsimultaneously caused to run in. The clear diazo-solution is made upwith NH: water to about 5 liters. An aqueous solution obtained from 239parts of 2-amino-8-hydroxyis H03s naphtha1ene--6-sulfonic acid andhaving an acid reaction towards litmus paper is then caused to wherein Rstands for the radical of a diphenyl n n, t a u 5 0-, W le vi r y ir inether and X1 and X2 stand for hydrogen, alkyl-, Stirring is continued,for one hour, at a temcycloalkylor aryl-groups, which may be conperatureof 30 C. and the Whole is filtered with nected inaheterocycljc ringsystem suction. By means of-sodium carbonate, the

I have found that valuable red monoazo dyedyestuff is transformed intothe sodium salt. stuffs soluble in water are obtained by coupling, Afterdrying, it is a red powder soluble in water in an acid solution, with2-amino-8-hydroxywhich y W001 fast Ted tintsnaphthalene-G-sulfonic acida diazo' compound (3) 344.5 parts of 4-amin04'-Ch10r0dipheny1 from anamino-diaryl ether substituted by the ether-Z-sulfodiethyl amide aredissolved in Water radical; and 300 parts of hydrochloric acid anddiazotized X, by means of 69 parts of sodium nitrite. An aqueoussolution obtained from 239 parts of2-amino-8-hydroxynaphthalene-6-sulfonic acid 2.5 and having an acidreaction towards litmus wherein X1 and X2 stand f 'v hydrogen, alkyl-,paper is caused to run into the diazo-solution yc y aridps, Which y be0011- thus obtained, at a temperature of 10 C.-15 C. ected n aheterocyclic ring Y Stirring is continued, for about one hour, at The wdyestuffs dye W001 fast Ted tints- C., and the reaction product isworked up as 5 They are d stin'gulshed from the lcnown azo dyeusual Thedy t fi is a red powder having Drop 30 Stuffs Obtamable by mfilm-60111130111? erties similar to those of the dyestufi described fromthe group of ammo-dlaryl ethers with in Example ammO'HaDhthOITSHHQmCacids or acylamino' If the amino-diaryl ethe-rs used in theprecednaphthol-sulfomc acids by a better fastness to mg examples are forinstance exchanged for getigpkrtocessing, partly also by a betterfastness one of the followiilg compounds: 35

The following examples serve to illustrate the 2-aminodiphenyletherl-sulfo-diethylamide, invention, but they are not intended to limitit 4-aminodiphenyl 'ether-2-sulfo-anilide, thereto; the parts are byWeight: i-aminodiphenyl ether-2-sulfo-ortho-toluidide, 7 4o (1) Asolution of 239 parts of 2-amino-8-hyl-aminodiphenyl ether- 2sulfo-N-ethyl-para- 40 droxynaphthalene-fi-sulfonic acid is acidifiedand chloranilide, then run while stirring into a diazo-solution ob-2-amino-4-chlorodiphenyl ether 4 sulfo (ii-- tained from 368 parts of4-amino-diphenyl ethermethylamide, 2sulfo-N-ethyl-anilide. The whole isfurther 4-aminodiphenyl ether-2-sulfo-piperidide, stirred for some hoursand worked up, after 4-aminodiphenyl ether-Z-sulfo-diphenylamide,complete coupling, in the usual manner. The 4-aminodiphenylether-Z-sulfo-nbutylamide, dyestuff is a red powder which dyes wool fast4-aminodiphenyl ether-Z-sulfo-cyclohexylamide, red tints, It correspondswith the following 4-amino-4-methoXy-diphenyl ether-Z-sulfamide,formula: l-amino-l'-methy1diphenyl ether 2 sulfo N mmethyl-ortho-toluidide, OH N=N 0- I Q 2-am1nod1phenyl ether-4-sul;fo-d1ethylam1de,

l-aminodiphenyl ether-3-sulfo-N-methylanilide, NR2 I l-aminodiphenylether-4-sulfo-dimethylamide, H 3 s O1.N\ Z-aminodiphenylether-3-sulfo-ethylamide,

3 can dyestufis having similar properties are obtained. 55

, 4 Claims.

The present invention relates to monoazo dyestuffs soluble in water;-more particularly it relates to dyestuffs corresponding with thefollowing general formula:

In Germany June 22, 1937 (2) A solution of 354 parts of l-aminodiphenylether-2-sulfo-N-methylanilide in 400 parts of glacial acetic acid isrun, while stirring, into 300 parts of hydrochloric acid and 300 partsof ice,

HOaS

wherein R stands for the radical of a diphenyl ether and X1 and X2 standfor members of the group consisting of hydrogen, alkyl, cycloalkyl andradicals of the benzene series, which may be connected in a piperidinering, being red-powders which dye wool fast red tints.

2. The water-soluble monoazo dyestuff of the following formula:

being a. red powder which dyes wool fast red tints.

3. The water-soluble monoazo dyestufi' of the following formula:

NH CH:

HOBS- S O LN being a red powder which dyes wool fast red tints.

4. The water-soluble monoazo dyestufi of th following formula:

SO2.N HOaS CgH5 being a red. powder which dyes wool fast red tints.

ERICH FISCHER.

